Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C57H65F5N10O8 |
Molecular Weight | 1113.1802 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CO[C@H](C)[C@H](NC(=O)OC)C(=O)N1CCC[C@H]1C2=NC3=CC([C@H]4CC[C@@H](N4C5=CC(F)=C(N6CCC(CC6)C7=CC=C(F)C=C7)C(F)=C5)C8=C(F)C=C9NC(=NC9=C8)[C@@H]%10CCCN%10C(=O)[C@@H](NC(=O)OC)[C@@H](C)OC)=C(F)C=C3N2
InChI
InChIKey=VJYSBPDEJWLKKJ-NLIMODCCSA-N
InChI=1S/C57H65F5N10O8/c1-29(77-3)49(67-56(75)79-5)54(73)70-19-7-9-47(70)52-63-41-25-35(37(59)27-43(41)65-52)45-15-16-46(72(45)34-23-39(61)51(40(62)24-34)69-21-17-32(18-22-69)31-11-13-33(58)14-12-31)36-26-42-44(28-38(36)60)66-53(64-42)48-10-8-20-71(48)55(74)50(30(2)78-4)68-57(76)80-6/h11-14,23-30,32,45-50H,7-10,15-22H2,1-6H3,(H,63,65)(H,64,66)(H,67,75)(H,68,76)/t29-,30-,45-,46-,47+,48+,49+,50+/m1/s1
Molecular Formula | C57H65F5N10O8 |
Molecular Weight | 1113.1802 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Pibrentasvir is a direct acting antiviral agent and Hepatitis C virus (HCV) NS5A inhibitor that targets the the viral RNA replication and viron assembly. NS5A is a phosphoprotein that plays an essential role in replication, assembly and maturation of infectious viral proteins. The basal phosphorylated form of NS5A, which is maintained by C-terminal serine cluster, is key in ensuring its interaction with the viral capsid protein, or the core protein. By blocking this interaction, pibrentasvir inhibits the assembly of proteins and production of mature HCV particles. In the United States and Europe, Pibrentasvir is approved for use with glecaprevir as the combination drug glecaprevir/pibrentasvir (trade name Mavyret in the US and Maviret in the EU) for the treatment of hepatitis C. This fixed-dose combination therapy was FDA-approved in August 2017 to treat adults with chronic hepatitis C virus (HCV) genotypes 1-6 without cirrhosis (liver disease) or with mild cirrhosis, including patients with moderate to severe kidney disease and those who are on dialysis.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3307224 |
0.0014 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | MAVYRET Approved UseMAVYRET is indicated for the treatment of adult patients with chronic hepatitis C virus (HCV)
genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh
A). MAVYRET is also indicated for the treatment of adult patients with HCV genotype 1
infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor
or an NS3/4A protease inhibitor (PI), but not both. Launch Date2017 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
324 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
600 mg 1 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
9.68 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
123 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
180 mg 1 times / day multiple, oral dose: 180 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
167 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
240 mg single, oral dose: 240 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.63 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
223 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
405 mg single, oral dose: 405 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
343 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
71.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
64.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
87.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
180 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2170 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
600 mg 1 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
54.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
881 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
180 mg 1 times / day multiple, oral dose: 180 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.56 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1040 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
240 mg single, oral dose: 240 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
118 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
16.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1630 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
405 mg single, oral dose: 405 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2560 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
408 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
474 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
594 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
600 mg 1 times / day multiple, oral dose: 600 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
21.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
22.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
180 mg 1 times / day multiple, oral dose: 180 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
16.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
240 mg single, oral dose: 240 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
14.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
12.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
17.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
405 mg single, oral dose: 405 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
14.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
16.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
17.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
14.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28464496 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
PIBRENTASVIR plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.1% |
unknown, oral |
PIBRENTASVIR plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
healthy, 18-55 years n = 8 Health Status: healthy Age Group: 18-55 years Sex: M+F Population Size: 8 Sources: |
|
600 mg single, oral Highest studied dose |
healthy, 18-55 years n = 6 Health Status: healthy Age Group: 18-55 years Sex: M+F Population Size: 6 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
In Vitro Antiviral Activity and Resistance Profile of the Next-Generation Hepatitis C Virus NS5A Inhibitor Pibrentasvir. | 2017 May |
|
Glecaprevir and Pibrentasvir in Patients with HCV and Severe Renal Impairment. | 2017 Oct 12 |
|
Efficacy of NS5A Inhibitors Against Hepatitis C Virus Genotypes 1-7 and Escape Variants. | 2018 Apr |
|
Integrated Resistance Analysis of CERTAIN-1 and CERTAIN-2 Studies in Hepatitis C Virus-Infected Patients Receiving Glecaprevir and Pibrentasvir in Japan. | 2018 Feb |
|
Glecaprevir + pibrentasvir (ABT493 + ABT-530) for the treatment of Hepatitis C. | 2018 Jan |
|
Efficacy of Glecaprevir/Pibrentasvir for 8 or 12 Weeks in Patients With Hepatitis C Virus Genotype 2, 4, 5, or 6 Infection Without Cirrhosis. | 2018 Mar |
Patents
Sample Use Guides
MAVYRET is a fixed-dose combination product containing glecaprevir 100 mg and pibrentasvir
40 mg in each tablet.
The recommended oral dosage of MAVYRET is three tablets (total daily dose: glecaprevir 300
mg and pibrentasvir 120 mg) taken once daily with food.
Route of Administration:
Oral
According to HCV replicon assays, pibrentasvir has EC50 values ranging from 0.08-4.6 nM agaisnt laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4d, 5a, and 6a, or EC50 values of 0.5-4.3 pM against laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4b, 4d, 5a, 6a, 6e and 6p.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:27:43 GMT 2023
by
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on
Sat Dec 16 09:27:43 GMT 2023
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Record UNII |
2WU922TK3L
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Record Status |
Validated (UNII)
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FDA ORPHAN DRUG |
550516
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NDF-RT |
N0000191256
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WHO-ATC |
J05AP57
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C166601
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100000166696
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1353900-92-1
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2WU922TK3L
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Pibrentasvir
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CD-35
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CHEMBL3545123
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Pibrentasvir
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Against HCV replicons containing NS5A from genotypes 1 to 6.
EC50
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Blood-to-Plasma Ratio | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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